2,3-SUBSTITUTED 2-AZANORBORNANES AS POLAR BETA-TURN MIMETICS

Authors
HORWELL DC NAYLOR D WILLEMS HMG
Citation
Dc. Horwell et al., 2,3-SUBSTITUTED 2-AZANORBORNANES AS POLAR BETA-TURN MIMETICS, Bioorganic & medicinal chemistry letters, 7(1), 1997, pp. 31-36
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Medicinal
Journal title
Bioorganic & medicinal chemistry letters → ACNP
ISSN journal
0960894X
Volume
7
Issue
1
Year of publication
1997
Pages
31 - 36
Database
ISI
SICI code
0960-894X(1997)7:1<31:22APBM>2.0.ZU;2-L
Abstract
The design and synthesis of -3-benzyl-2-azabicyclo[2.2.1]heptane-2-car boxamide (3) as a conformationally constrained non-peptide beta-turn m imetic is described. Compound 3 is shown to mimic the Trp and Phe side chain conformation and the overall dipole moment of MEN10627 (2), a c yclic hexapeptide with a high NK-2 affinity. The tachykinin receptor a ffinities of 3 are evaluated and compared to those of MEN10627 and pre viously reported Trp-Phe mimetic 1. Copyright (C) 1996 Elsevier Scienc e Ltd